Interpolymerization products of butadiene and a vinyl ethinyl carbinol



Patented May 14,

UNITED STATES INTERPOLYMERIZATION PRODUCTS BUTADIENE AND CARBINOL OF AVINYL ETHINYL Wilhelm Sandhaas, Mannheim, Walter Daniel,Ludwigshaien-on-the-Rhine, and Kornelius Miihlhausen, Leverkusen,Germany, assignors to I. G. Farbenindustrie Aktiengesellschatt,FrankIort-on-the-Main, Germany No Drawing. Application January 3, 1938,Se-

rial No. 183,120.

4 Claims.

The present invention relates to rubber-like interpolymerizationproducts and a process of producing same. I a

It is already known that vinyl ethinyl carbinols can be polymerized andthereby first yield soft 5 substances capable of extension somewhat likerubber, which are converted into hard, brittle products when heated. Thelatter, contrasted with the rubber-like polymerization products firstobtained, are insoluble in organic solvents, such as for example benzineand benzene.

We have now found that rubber-like, stable polymerization products whichare also insoluble in organic solvents are obtained by polymerizing inemulsion mixtures of butadiene and vinyl ethinyl carbinols. The vinylethinyl carbinols may be obtained in knownmanner by the action of vinylacetylene on aldehydes or ketones according to the followingreaction':---

B being hydrogen or an aliphatic, cycloaliphatic, aliphatic-aromatic,aromatic or heterocyclic radicle and R1 being an aliphatic,cycloaliphatic,

The polymerization products obtained have good mechanical properties andare practically insoluble in organic solvents, in particular benzine,benzene and lubricatingoils. In addition to the purposes for whichnatural rubber is suitable, they may also be used for purposes whereresistance to organic solvents, in particular to motor fuels andlubricating oils, is required. The interpolymerization products maybemixed with fillers and dyestuffs in the manner usuaiin the 8 rubberindustry and may be vulcanized, after the addition or vulcanizingagents, vulcanization ac- In Germany January 5,

celerators and if desired agents protecting against ageing, to formarticles similar to soft or hard rubber.

The following example will further illustrate how this invention may becarried out in practice but the invention is not restricted to thisexample. The parts are by weight.

Example parts of butadiene and 25 parts of vinyl ethinyl dimethylcarbinol are emulsified with 150 parts of a 10 per cent aqueous solutionof oleic acid sodium salt and after the addition of 0.35 part ofammonium persulphate the whole is kept at 30 C. for hours. After addinga small amount of phenyl beta-naphthyl amine dissolved in benzene ordispersed in water the interpolymerization product formed may becoagulated from the aqueous dispersion by an addition of sodium chlorideand acetic acid, an elastic plastic mass being obtained. It yields whenvulcanized rubber-dike masses having excellent mechanical properties andbeing insoluble in gasoline, benzene and lubricatingoils.

What we claim is: i i 1 1. .The process of producing rubber-likeinterpolymerization products which comprises polymerizing a mixture ofabout three parts of butadiene andone part of vinyl ethinyl dlmethylcarbinol in aqueous emulsion.

2. Rubber-like interpolymerization products of butadiene and vinylethinyl dimethyl carblnol, substantially identical with the productsobtained by the process defined in claim 1.

3. A process of producing rubber-like interpolymerization products whichcomprises polymerizing a mixture of about three parts of butadiene andone part of a vinyl ethinyl carbinol WILHELM' SANDHAAS.

WALTER DANIEL. Y KORNELIUS MUHIJ'IAUSER-

